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Reaction of nitrones with trimethylsilylketene

✍ Scribed by Kiyo Takaoka; Toyohiko Aoyama; Takayuki Shioiri

Book ID
104261201
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
178 KB
Volume
40
Category
Article
ISSN
0040-4039

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ChemInform Abstract: Reaction of Nitrone
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Reaction of Nitrones with Trimethylsilylketene. -Trimethylsilylketene reacts smoothly with diarylnitrones (I) to give oxindoles. Mixtures of N,N-diacylamines (V) and N-acylamines (VI) are formed with N-arylmethylnitrones (IV). The mechanism is discussed. -(TAKAOKA,

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The reaction of nitrones with various indole derivatives has been studied. When the reaction was promoted by ClSiMe 3 , the isolated products were 3,3 H -diindolylalkanes. With HCl as the activating reagent, 3-indolylhydroxylamines were isolated. The diastereoselectivity of this condensation with a

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N-(Benzylidene)-and N-(2-phenylamino-2-oxoethylidene)aniline N-oxides add stereospecifically to the double bond in 4-methylene-and 4-acryloylamino-4-methyltetrahydropyrans to give substituted isoxazolidines. The use of 4-methyl-5-arylamino-and 4-arylaminomethyl-5,6-dihydro-2H-pyrans for the synthesi